My Favorite Boss Pt. 01

It started two years ago, when I was 21. I had just finished my sophomore year at the University of North Carolina and had decided I wanted to work in real estate. This summer was the first I was trying to live alone: growing up, I lived with my mom and my two sisters, so I was more than ready to have my own place.

I guess I should share a bit about myself. My name is Blake, and I'm gay. I knew I was gay for pretty much my whole life, but only came out towards the very end of high school. My family was a little surprised at first, because I guess I present as more masculine and always played sports, but they were totally accepting. Speaking of sports, I'll say I'm proud of my physique. I'm 5'11", about 185 lbs, and have short, light brown hair. As a kid, I was kind of chubby, so when I got into high school I really focused on weightlifting and training, and I've maintained that lifestyle. I have a German build, so I'm a bit stocky and hairy, but I like the way I look in the mirror. I have broad shoulders, a chest that sticks out further than my belly, defined arms and abs, and powerful legs. As a gay man, I'll also say I'm blessed with a bit of a natural bubble butt - nothing crazy, like you see on those Instagram gay models, but I fill out a pair of pants nicely.

Anyways, I was 21 and going into real estate. I had looked for a local summer internship and ended up interviewing for one in Charlotte. It was with a private contractor and home builder who did a lot of cool custom homes, and I thought I could learn a lot from him. From his website, he'd worked on some beautiful projects, and from the online interview, he seemed nice. He ran a small business, with only himself and his assistant, so I'd also get good experience from that. Charlotte was about 3 hours away from where my family lived in Raleigh, though, so I found the cheapest apartment on Air B&B I could find and moved up there to work for the summer.

I started the day after I moved to town. That morning, I got up extra early to shower and get dressed, hoping to make a good first impression. "Peller Custom Homes" was written on the icy glass on the second-floor office door. I took a quick picture of the door and sent it to my family, took a deep breath in, and knocked lightly on the door at 8:55 AM.

"Coming!" a female voice called from within. A woman answered the door. "Hi! You must be Blake! I'm Kathryn, I'm Mr. Peller's assistant."

She invited me inside. The office was small, only one room. In the corner to my right was Kathryn's desk, which was adorned with a few family photographs, as well as an orchid. To my left was a small couch and coffee table, presumably a waiting area. The back half of the office appeared to be Mr. Peller's desk, with tubes of blueprints stacked up high behind it from his many projects. On the wall hung several awards he had won, such as the "Custom Home Builder of the Year." He also had a large Clemson pendant hanging above his desk.

Kathryn and I briefly talked, and she explained that her daughter was in school that was around my age. Kathryn worked for Mr. Peller during the school year to save up money, and during the summer she took her daughter traveling to somewhere exotic with their savings. "Mr. Peller, or, he'll probably just want you to call him Carson. Anyways, Carson won't be in until noon, as he's checking on some projects. Until then, let me show you the systems."

Kathryn spent the morning explaining what my responsibilities would be that summer. She said she normally likes to get to the office early to make coffee and tidy up. She kept track of the boss's meetings and tracked the deliveries of custom orders to projects they were working on. For example, if they placed an order for custom cabinets on a Monday, she'd call and confirm measurements on Tuesday, and check on their progress every three days until delivery. She said she was friends with most of their contacts, and that they'd be happy to answer any questions I might have.

They went over things and talked until, around 12:15, a man walked through the door. "Hey, Kathryn. And you must be Blake! I'm Carson." the man said, with a big grin on his face. Carson is about 6 feet tall, with dark brown hair and a full beard on his face. He had kind brown eyes and a winning, warm smile. Physically, he had a large presence - he was bulky and muscular, as Blake could see the outline of his firm pecs through his collared shirt and his big biceps stretched his sleeves. Dark chest hairs poked out of the top of his shirt. He had a bit of a beer belly, but Blake could tell he also had a tight, solid core. He wore fitted khakis and new tennis shoes. He stuck out his hand.

I shook his hand and smiled back. "Blake," I responded, and noted his firm but friendly handshake.

"Nice to meet you, Blake," he said. "Kathryn, let's all go out to lunch, my treat."

We went to a nearby deli within walking distance, and Carson asked me questions about myself. "You're interested in real-estate, right?" he asked, and I nodded. "Well, I'll help you learn as much as I can this summer."

Kathryn explained what we'd gone over that morning, and he seemed impressed. Kathryn would be around all week, showing me the systems, then starting the next Monday I'd be on my own. We all made sure to exchange contact information.

"So, Blake, you into sports?" Carson asked.

"Yeah," I said. "I played football and baseball in high school, and in college I've been playing on intramural teams, too."

"A football guy!" Carson said. "I played football, too. Now I play rugby with a local team. Do you know how to play rugby?"

"No, I've never played."

"Well, I'll have to explain it sometime," Carson said. They continued to talk, and Carson seemed legitimately interested in me, not just as an employee, but as a person. "You could come watch one of my games."

They returned to the office, and Kathryn continued to explain her systems the rest of the afternoon. It was a lot to take in, as Kathryn seemed to be a very organized person. I, on the other hand, was kind of a slob at home, so I was paying extra attention to everything she did. I wanted to do well at this job, because I knew it could lead to some great opportunities.

At the end of the day, at 5, we all wrapped up around the same time. As we walked towards the door, I glanced again at Carson's body. His large, muscular-bear build caught my eye as he walked towards me. We made eye contact as I snuck a look at him, but quickly looked away, not wanting to seem weird. He chuckled, and we said goodbye for the day.

I got home and logged onto my computer. I looked over all the calendars that Kathryn kept again and compared them to my notes to remind myself. I thought it would make Kathryn happy if she knew she was leaving the business in good hands, so I needed to understand everything as quickly as possible.

That night, as I got ready for bed, I felt a little horny. I looked up some porn on my phone and whacked off. Before college, I hadn't had any gay experiences, but I wet my whistle pretty quickly. I was actually kind of a slut my freshman year: I became known as almost a community cocksucker. I didn't join a frat, but I still had plenty of dudes who came to me wanting their dicks sucked, and most would suck me back. My sophomore year, I settled down and got a boyfriend, Danny, who I was still dating. We were trying to do long distance that summer, but neither of us were great communicators, so we didn't talk often. Still, we had been exclusive, and I didn't have any plans to break that commitment.

The rest of the week was just more of absorbing Kathryn's processes. There was a distinct method to her madness that, after a while, became intuitive to me. By Friday, she felt comfortable leaving me in charge half-way through the day, as I'd mastered her system. We'd also traveled with Carson to a couple of houses he was overseeing, and I learned what he wanted me to take notes on while there. I was getting paid $20 an hour, which was sweet change, and more than covered my rent.

They job seemed perfect, except for the times that I got caught looking at Carson. I felt like we made eye contact an uncomfortable number of times - he'd catch me staring at him and smile back at me several times a day. I always got embarrassed and looked away, but it didn't stop me from looking back again. Going into the weekend, I decided I was going to focus at work and keep my eyes on my work.

Starting the next Monday, I was alone in the office with Carson. He greeted me warmly and went about his work when he came into the office. I had done as Kathryn did and made coffee, which he thanked me for. Carson was a handsy guy - always patting me on the back, giving me a fist bump, and just standing close to me when we were looking at something on the computer together, I always got a bit nervous when we were in the same space.

For most of that week, though, I kept it professional. I called my family and told them how well I was doing, and even called Danny to tell him all about the new job and apartment. It was all going well - until Friday morning.

Friday morning, on my second week of work, I realized my tire light was on while I was driving to work. I safely got to the parking lot, but when I checked my tires, I realized one of my tires was almost completely flat.

It didn't take me long to find a nail hole in the tire. I'd never changed a tire in my life, and just stood by my car helplessly for a moment, looking up YouTube videos on it. That's when Carson pulled into the parking lot.

"Hey, what's up?" he asked. "Ooh, nasty flat," he said.

"Yeah," I said.

"Do you need help swapping it out? We can get it done real quick, so you don't have to worry about it. You'll have to get it replaced soon, though."

"That'd be great, actually," I said. "Unless you have work to get to, that's totally okay."

"No sweat, we can get it done quick. Get the spare out of the trunk."

We went around to the trunk, and Carson explained to me how to change a tire. He showed me how to do it, then let me do most of the work. "Thanks for taking the time to teach me, Carson," I said as we loaded my popped tire into my trunk.

"No problem," he said with his signature smile. "Happy to help."

I smiled back, then noticed he had a big grease stain on his white dress shirt. "Uh, I think you got some grease on your shirt."

"Oh fuck," he said, looking down. "Wait, shit..." he walked back to his car, and looked in the back seat. "Damn, I have a meeting with an important client today, I can't wear this... Quick, give me your shirt."

"What?" I asked, taken back.

"Yeah, I have a gym shirt you can wear, I just need a clean shirt," he said, taking his off. I stared at his manly chest for a second. His manly bear chest caught my gaze, as his masculine figure reached out his hand to me. Following instructions, I took off my shirt and passed it to him, and he slipped it on. He threw me a gym shirt.

"Damn, this smells awful," I say as I laugh. It's a muscle shirt with the sides cut almost all the way down the sides of the shirt.

"Sorry," he said, laughing with me. "It's all I've got."

"It's okay," I said. "Fair trade for you helping me fix my tire."

Carson chuckled. "I guess we're even then." We walked inside, but I took a moment in the restroom to smell his shirt. His sweaty musk was all over it, and I couldn't help touching myself as I breathed in his stink. I was still at work, though, so I tried to put it out of my mind and quickly went back to my desk.

Carson went to his important meeting, and he got back to the office around 5, just in time to lock up. "Hey! Meeting went well, I'll send you my notes," he said. "Here, let's swap shirts back."

I was a little bummed that I didn't get to take this home for the weekend, because I'd been fantasizing about jerking off in it all day long. But I traded back regardless and was glad when I put my own collared shirt back on, it smelled a bit like him, too. He slid his workout tank on, and I loved that I could see so much of his torso through the sides of the shirt.

"Alright, let's lock up," Carson said. "Thanks again for the shirt swap, man. You saved my biscuit."

He smiled at me, and I smiled back. "Any time."

I had to make a few stops on the way back home. I dropped off Carson's collared shirt at the dry cleaners, hoping they could work a miracle, picked up some things for my apartment, and finally stopped for cheap Chinese food before hopping back on the way home. By the time it was dark, I was halfway home, and I stopped for some gas at a station on the side of the road.

As I filled up, I smelled my shirt again, breathing in what was left of Carson's masculine scent. I'd never gone for older guys, but something about him was just making me tick. For a moment, I felt guilty about being so turned on by someone other than my boyfriend, but in the moment I couldn't think of much else. At the pump, I looked around to make sure no one was around before I ran my hand over my cock in my pants a few times, preparing for the massive jerk off session I was going to have as soon as I got home.

Just then, I heard a familiar voice. "Blake?" it said, and I turned to see Carson walking towards me.

"Carson? What are you doing here?" I asked, blushing and trying to conceal my growing hardon with my hand. Carson was still in the same outfit from work.

"I live right down the street, came to get some beer," he said. "Small world."

"Yeah," I said, laughing a bit nervously. Carson had come over and put his arm up on the side of my car, leaning casually. His wide figure standing over me didn't help to conceal my growing boner. "Small world," I said as I put the pump back.

"Hey, thanks for swapping shirts with me again," he said, punching me lightly on the shoulder. One of his hands was on my car, and the other was on his belt. His smile and laugh put me at ease. "I thought on the way home, I would have had a much worse day if I swapped shirts with Kathryn."

I laughed. "Yeah, you squeezing into one of her blouses would be a sight," I said, laughing. I'd finished pumping, but I didn't move to get in my car just yet. For a moment, I imagined him stretching the buttons on a woman's shirt, but quickly put it out of my mind.

Carson laughed too. "Yeah, that would be something," he said. We stood there for a moment, in silence, looking at each other. He looked down, probably seeing the bulge in my pants, at the same time I looked down and glanced at his. Through his pants I could see a growth pushing his zipper towards me, and my heart raced. Was he turned on by me, too?

We stood there for a moment in silence, looking each other up and down, before Carson finally broke the silence. "Hey..." he whispered, "Why don't you move your car over towards mine?" He pointed to his truck on the other side of the gas station, in a dark corner under some trees.

"Sure," I said quickly, and before I could think about what I was doing, moved my car over and parked next to his. He'd walked over, and we met between the cars. My heart was pounding in my ears, and my stomach turned with excitement.

"Hey," I said. I noticed he'd undone his belt and his top button of his pants.

"Hey," he said back. He opened the door to the back seat of his truck. "You know, it's been a long day... You want to suck me in the back seat of my truck?" he asked confidently. Stunned, all I could do was smile and hop in.

I climbed in first, and he climbed in after me and shut the door. His truck was big, so he had space to lay out as I got on the floor and unzipped his pants. It was dark and I couldn't see well, but knew he had a good cock as I took it in my mouth. His head was dribbling precum before I even kissed it, and as I wrapped my lips around his solid girth. I pushed his dick deeper into my mouth, showing off what I'd "studied" in college. He was about six inches long, the perfect length for a boyfriend. I ran my hand up his thigh and to his chest as I sucked him, and he ran his fingers through my hair as I bobbed up and down on his manhood. My cock throbbed in my pants, begging to be released. I got goosebumps as his hand touched my face.

His soft moaning made me crazy, and I finally freed my dick from my pants and jerked off as I continued to work over Carson's dick. "Yeah, suck me..." he whispered under his breath. I cupped his heavy balls with my hand as I sucked, and after about five minutes, I could feel his breath getting faster. "Fuck, I'm getting close," he said.

I buckled down and kept going down on his dick. The next moment, he shot his warm, salty spunk into my mouth. I wish I could have kept it in my mouth longer, letting its salty flavor coat my tongue and blend with my saliva, but I couldn't stop myself from hungrily swallowing it.

He grabbed my shirt and pushed me back on the seat before he got down and started sucking me. I'm about 7 inches hard, but not quite as thick as Carson. His tongue ran around the head of my dick so tenderly that I could hardly contain myself, as I muffled a loud moan. He ran his hands up and down my legs as he sucked on me, squeezing my flesh as I softly moaned. His big, powerful hands ran up the sides of my legs and he touched the sides of my ass, and my eyes rolled back as I felt his beard tickling my cock. I couldn't last long - I'd been needing to bust all day. After about two minutes, I told him I was about to cum, and he returned my favor and sucked me to completion. I let out a huge load, which he swallowed in full.

We sat back for a moment, both catching our breath, before we put our pants back on without a word. I got out of his car, and once again we met in between them. "Thanks," we said at the same time, and giggled. "Have a good weekend," he said, and he got in his truck and left. In the dim parking lot light, I couldn't quite make out his expression. I watched him drive away and sat in my car for a moment.

On the drive home and for the rest of the night, I couldn't stop thinking about the encounter. Half of me was consumed by regret - had I jeopardized the perfect job by giving into my desires? Will work be forever awkward? I thought about Danny, who I'd just cheated on, and thought about how hurt he might be if he found out. The other half of me, though, was still glowing from the feeling of Carson's hands running up and down my body. I felt his warmth in my mouth and his hands on my legs all over again and couldn't fully feel like what I did was wrong, because it felt so right. I finally got to sleep after hours of wondering if I'd just ruined my summer, or if it was just getting started.